[Moneyking]

Dimethyl ether is the product of methanol plus mineral acid. This is because the oxygen is protonated and becomes a leaving group. The oxygen of another methanol will substitute the protonated oxygen to product water and dimethyl ether. You need to know that is how the reaction works. Therefore, if two different alcohols were used, you would get a mixture.

Ok so, sulfiric acid + methanol = dimethyl ether?
"Therefore, if two different alcohols were used, you would get a mixture."
what do you mean by that?

[Arkcon]

So, pick two alcohols:  say methanol and ethanol, if you make ethers with sulfuric acid, what ethers do you suspect you'll get?  Do you expect just dimethyl ether and diethyl ether?

[Borek]

Imagine you have a pocket full of black and white marbles. You take two at random. Do you expect to draw always two identical ones?

[Moneyking]

So, pick two alcohols:  say methanol and ethanol, if you make ethers with sulfuric acid, what ethers do you suspect you'll get?  Do you expect just dimethyl ether and diethyl ether?

you will get random, either dimethyl ether, or diethyl ether. is that correct?

[Borek]

So you will never draw one white and one black?

[Moneyking]

So you will never draw one white and one black?

lol i was answering the other dudes question, and for yours, you won't always draw 2 black or 2 white, sometimes you will draw one white and one black.
say 10 balls, 5 black and 5 white, the % of getting 1 white and 1 black is greater than getting 2 blacks and 2 whites.
(1/2)*(4/9)0.44 for 2 blacks or 2 whites, and the other equation is (1/2)*(5/9)=0.55
getting 1 white and 1 black is slightly higher.

[Borek]

you will get random, either dimethyl ether, or diethyl ether. is that correct?

and for yours, you won't always draw 2 black or 2 white, sometimes you will draw one white and one black.

And you still don't see what is the problem here?

[Moneyking]

you will get random, either dimethyl ether, or diethyl ether. is that correct?

and for yours, you won't always draw 2 black or 2 white, sometimes you will draw one white and one black.

And you still don't see what is the problem here?

umm, i think the problem is we don't know the output?

[DrCMS]

umm, i think the problem is we don't know the output?

No the problem is you have not listened for even one second to what people have been trying to tell you helpfully for the last 4 days. 

Start with mixture of alcohols and you will get a mixture of symmetrical and unsymmetrical ethers.

If you react methanol with sulphuric acid you get dimethyl ether and if you react ethanol with sulphuric acid you get diethyl ether.

But if you react a mixture of methanol and ethanol with sulphuric acid you get a mixture of dimethyl ether, diethyl ether and methoxyethane.

[Moneyking]

umm, i think the problem is we don't know the output?

No the problem is you have not listened for even one second to what people have been trying to tell you helpfully for the last 4 days. 

Start with mixture of alcohols and you will get a mixture of symmetrical and unsymmetrical ethers.

If you react methanol with sulphuric acid you get dimethyl ether and if you react ethanol with sulphuric acid you get diethyl ether.

But if you react a mixture of methanol and ethanol with sulphuric acid you get a mixture of dimethyl ether, diethyl ether and methoxyethane.

how do you get methoxyethane from that mixture?

[Arkcon]

how do you get methoxyethane from that mixture?

One white ball and one black ball.  Like DrCMS: said, this has been an issue this entire thread: you keep saying you understand that you never know which two will end up coupled by an ether link, yet you consistently forget that you might get an ether with mixed groups.

[Moneyking]

how do you get methoxyethane from that mixture?

One white ball and one black ball.  Like DrCMS: said, this has been an issue this entire thread: you keep saying you understand that you never know which two will end up coupled by an ether link, yet you consistently forget that you might get an ether with mixed groups.

ok, so what you are saying is you can either get dimethyl ether, or diethyl ether or methoxyethane right? not all 3 of them in just one reaction?

[DrCMS]

how do you get methoxyethane from that mixture?

One white ball and one black ball.  Like DrCMS: said, this has been an issue this entire thread: you keep saying you understand that you never know which two will end up coupled by an ether link, yet you consistently forget that you might get an ether with mixed groups.

ok, so what you are saying is you can either get dimethyl ether, or diethyl ether or methoxyethane right? not all 3 of them in just one reaction?

NO NO NO!!!

What every person trying to help you has been saying right from the start is that you will get a mixture of all three products.

[orgopete]

Imagine you have a pocket full of black and white marbles. You take two at random. Do you expect to draw always two identical ones?

I rather liked this example. I wish I had thought of it. I thought it explained getting a mixture of products without telling the poster he would get a mixture of products.

[Moneyking]

Imagine you have a pocket full of black and white marbles. You take two at random. Do you expect to draw always two identical ones?

I rather liked this example. I wish I had thought of it. I thought it explained getting a mixture of products without telling the poster he would get a mixture of products.

how is that possible? where do the extra Carbons come from?